This paper appreciates the role of tourism within the more holistic framework of urban policy in the context of coastal cities. Through an investigation of two medium-sized Italian cities (Rimini and Pesaro), the study addresses the paucity of literature on regeneration strategies conducted in coastal areas where tourism has already reached a mature stage of development. The idea of a “culture city” emerges as the most appropriate pathway to innovation, change and progress in line with the several, albeit often criticized, examples of culture-led regeneration in urban studies. The discourse analysis of the strategic plans of each city emphasizes the different role that the sea and the seaside play in each location. Rimini explicitly includes these factors as pivotal cultural resources, which is evident in the innovative concept of “sea wellness”. Pesaro, on the other hand, does not attribute a specific role to the sea and the seaside; they are instead simply juxtaposed with a vibrant city centre that appeals to business and cultural tourists.